Satoko
by Sharreezy
Summary: Ash isn't a cross dresser and the times he has cross dressed are because of important situations that needed him to do so, on the other side Shigeru doesn't really seem bothered by this. Compilation of One Shots about the times Ash had cross dressed in the anime and how his boyfriend reacts to each time.


Satoshi isn't a cross dresser.

It's not that there was something bad about being one, he was a really open minded person and however other people wanted to look or act was their business, not his, as long as they had a good soul then that's all that mattered.

But this time he had to cross dress in order to get into a gym and win a damn badge, god, he really wanted to win it and Team Rocket had offered help. Yes, Team Rocket. Which was incredibly strange of them but hey, Ash was in need and there was nowhere else where he could get girl clothes without having to ask one of his friends.

That would be embarrassing.

And probably they wouldn't stop teasing him about it if they knew, so Team Rocket was really necessary in this _particular_ situation.

He didn't know why but they carried _alot_ of costumes in their balloon, of every kind.

So now he was sitting in the balloon, looking at himself in a golden hand mirror as James was brushing his long, blonde wig, which looked pretty real, it was probably made out of natural, human hair and also was pretty long, the golden hair reached his waist even when it was curled at the ends and he was also wearing a big, pink bow on the top of his head which made him look even more girly.

-"I think it's good enough like this, James"- The trainer whispered with a little frown, this was taking longer than expected and sitting here was plain boring, then noticed the blue haired man brush continuing to brush the blonde bangs on his forehead to keep them in place.

-"Hey, do you want them to really buy that you're a girl? Then let me make you look good enough for that"- He replied and Ash couldn't really argue with that logic, he stayed quiet while patting Pikachu's head as the pokemon was sleeping in his arms.

Twenty minutes later his "costume" was ready: he was wearing a long orange dress that reached right under his knees and fitted him really good on him since it was tight on the torso, making it look very small since Ash was so thin, his waist looked even smaller giving him the femenine look that he needed. It also had white, lace details right at the very ends of the skirt and the sleeves that only covered Ash's shoulders and half of his upper arm.

It was such a beautiful dress, he must admit it but why on earth would Team Rocket use this? Jesy was much taller than him and the dress wouldn't really fit her and James wasn't thin enough to wear it.

-"Now the final touch"- Jessie said taking a blue bow that had a ruby on the center, placing it on the white neck of the dress.

-"He isn't ready yet, Jess"- He heard James mumble as he walked towards Ash, curling his lashes and applying a light coat of mascara, then some lip gloss and slight blush on the top of Ash's cheeks. - "Now he is!"- he said raising his hands excitedly - " You look beautiful Satoko!"

-"Satoko...Uhm...Well! thank you Team Rocket I...I don't even know why you guys are being kind to me this time but...Thanks"- Ash said with a sweet smile as he was putting on the red shoes that had a little heel, god he did look like a lady, James thought while looking at the blonde girl that was standing now before them.

Obviously Team Rocket didn't do this because they suddenly wanted to help Ash or become kind, they simply did it because it was a good way of keeping Ash distracted so they could enter the gym and steal all the pokemon, which as always didn't work and after Ash earned his badge, he sent them through the air to some other place.

-"Thank god they're out"- Ash mumbled under his breath as he walked outside the gym with a tired Pikachu resting over his shoulders, it was noon and getting dark so he probably should go back to the pokemon center where Brock and Ritchie were waiting for him, his friends were there because if they came with him this time they would've been recognized and finding out Ash was a boy would've been easier.

-"Ash..."- Satoshi heard a voice coming from the bushes and Pikachu lifted his ears at the suspicious sound, the amber eyed boy saw a very handsome guy he knew really well, Shigeru, who was standing right there with a weird smirk on his face, it wasn't the usual cocky smirk, this one was different.

 _Fuck no._

\- "Shi-Shigeru!"- Ash said nervously, oh god, his boyfriend was totally gonna think he's a freak! and probably would want to break up! Here he was dressed as a girl and tryng to cover his obvious orange dress with his hands but couldn't really help the blush and heat that went up to his cheeks, he was so embarrased and Gary would most likely break up with him and think he's weird. - "I-I can explain!"-

The predatory emerald eyes moved up and down on Ash's delicate frame, he licked his lips as he realized how well that dress suited him. Ash's neck, shoulders and arms were really slim but were usually covered by some oversized clothing, not this time though and it made him look even more delicate, his body had some curves, like a really small waist and nice hips and this was showing amazingly thanks to the dress. Oh well now Gary was moving like a lion when trying to catch a zebra, he grabbed Ash by the waist and lost all control of himself not even caring that poor Pikachu jumped off Ash's shoulders to stay right next to them, covering his eyes with his paws.

Pikachu knew what Gary will do with it's master, it wasn't the first time they did this but usually when they did Umbreon was around so they could play, not this time though, which made the pokemon stand next to them covering it's eyes.

It was too much for Gary to see Ash's soft yet firm legs exposed like this when he lifted the dress, it was way too much to see him moving and speaking like a delicate girl does and doing it so well. Fuck, it didn't even sound forced and this was doing wonders for Gary's mind and cock. -"Shhh... C'mon baby girl"- he whispered right against the younger boy's ears, placing little kisses under it and making Ash shake in pleasure, feeling him place one of his thin hands over Gary's bicep. -"Be good, alright?"- he said, moving his own hands up on the back of the black haired's thighs to squeeze his bum, even when Ash didn't had a huge ass, he did had a perky, perfect bum and it was more than enough for Gary.

The young trainer didn't know how to react, it wasn't the first time his boyfriend touched him like this at all and actually, they had an active sexual life but he was now dressed as a girl and he would've never thought how hard that could make Gary this horny that he forgot they were in a public street. - " S-Shigeru...n-not right here, S-Shigeru!"- He gasped feeling a long finger entering his tight hole.

-" Calm down...just let me enjoy you baby girl"- Gary whispered in that seductive tone of his, grinding his hard boner against Ash's thin and soft thigh, Satoshi knew his boyfriend was smirking, oh god he hated that horny smirk. -"Mmm someone is really tight"- he kept moving his finger against the nerves in Ash's sweet spot, in and out of him, making his knees shake until Ash slided down the floor not able to support his own weight anymore, panting and moaning and also trying to cover his mouth to not be so loud, after all they were still in a public place.

Ash was all his, Gary thought as he kneeled infront of the boy right between his legs, he then moved his free hand to unzip the back of dress, letting it hang low and exposing Ash's thin shoulders, he bite down on the skin over the collarbones that were showing, leaving some hickeys then felt a pair of delicate hands push him away by the chest, not strong enough to hurt him or make him fall but enough for him to stop.

-"S-Shigeru not here"- Ash said looking up into the emerald eyes, a vibrant pink blush was showing on his tanned cheeks and even when his voice was shaky because of all the pleasure his boyfriend was giving him, he didn't want to be fucked in the streets, doesn't matter how horny he was.

-"Fine, princess"- Gary nodded and passed an arm under Ash's knees and another under his back, lifting the raven haired and currently blonde easily, Ash was really light, carrying him to a hotel that was close to where they were, Shigeru didn't care if he had to pay 700 dollars for a room in order to fuck Satoshi, god he was so horny and walking with a throbbing erection wasn't nice at all.

Pikachu raised his ears as he noticed Gary carrying his master and followed them.

The action made Satoshi blush, it wasn't the first time Shigeru carried him like this and he wasn't complaining about it but the fact that his dress was still unzipped and looking messy and how people were staring at him made him feel quiet embarrassed, couldn't Gary take him to the hotel and then attempt to fuck him? did it have to be on the street? Ash sighed, he knew in situations like these his boyfriend lost all control of himself.

Once they arrived into the beautiful and luxurious looking hotel, Shigeru paid for the room and yeah, it was fucking expensive for a night but being a researcher paid well, so he didn't really mind that much.

Once they entered the hotel room Gary continued what he was doing and sat down on bed with Ash on his lap, making the younger one stare at him with a small smile showing on his lips and hands cupping Gary's pale cheeks.

Pikachu ran into the room and wondered around until he found a small room meant for pokemon, he squealed happily at the amount of toys that were there and started playing, totally forgetting about that horny researcher who was trying to touch it's master.

Back to the couple, Gary's hands were sliding under the skirt of the dress enjoying the touch of perfectly toned thighs as he pulled the top of the dress lower with his teeth, now exposing Ash's pink nipples, he leaned forward and sucked on one, moving his tongue around it as Ash panted and stroked the auburn hair.

Gary smirked once again, he loved to hear Ash moaning and see the faces he made, it was art.

The black haired felt as if he could finally relax and give in to his boyfriend's lustful wishes, his blush wasn't artificial anymore and it looked even more intense at the top of his cheeks, his eyes were closed and pink lips coated in lip gloss were open.

Gary looked up, blissed by the view and wrapped one of his hands around Ash's small waist, pulling him in for a long, passionately sweet kiss, tasting his cherry lips and entering his mouth with his tongue.

-"mmm..."- The amber eyed hummed in response as he felt Shigeru's tongue take dominance of his mouth, rubbing their tongues together deliciously, it made Ash's back arch from pleasure. He loved when Gary kissed him like this and to keep him closer, he lifted his hands and slided his fingers through the auburn hair, making Gary shiver and pull him into his body, Ash's flat and thin belly was touching with Gary's abs.

-"What are you doing to me, Satoshi"- He panted huskily, pulling away from the kiss slightly only to breath and then continued kissing his boyfriend even more passionately. And sometimes Gary really wondered what was Ash doing to him, he has never been like this with anybody, he never lost total control of himself and he never, ever gave up his pride in order to please someone else, it didn't matter how hot the chick he was fucking was or how good the fuck with a guy could be, he didn't lose any of these things.

Yet with Ash everything was different and Gary couldn't even feel bad about it. He didn't care if he looked like a dog following him around, he didn't care if his brain was screaming at him for being so stupidly in love, Ash was worth all of this.

The black haired, currently blonde, boy couldn't help but blush at the question. He made Gary motherfucking Oak out of all people lose total control over himself and that was something to be proud of. He slided his hands down to Gary's neck and then up again, cupping his face in an affectionate manner and pulled away from the kiss only to look into his eyes.- "Loving you, Shigeru, that's all I'm doing"- He said in such a sweet whisper that made Gary want to kneel and ask Ash for marriage right now, he smiled and turned his face to kiss the center of his right palm, taking the hand softly and kissing the back of it also.

And at that very moment the only thing that mattered in the world were them, their eyes were connected showing the strong bond that will keep them together for eternity and like a Yin Yang,Ash was the sweet side Gary lacked and Gary was the aggresive and more determined side Ash needed to be complete, they needed eachother as our bodies need water to survive.

Ash moved his other hand and stroked Shigeru's cheek with his thumb, pulling him in for another kiss, Satoshi slowly started moving his hips in circles over his boyfriend's crotch, making him react by bucking his own up into the black haired's. - "I need you inside me, Shigeru"- Ash whispered into his ears while sliding his hand up under Gary's purple shirt, touching his toned chest. -"Please"-

It took Gary no time to take his shirt off and unzip his jeans, he stood up carrying Satoshi once again and settling him down on the black table that was in the room for decoration, he opened the trainer's legs and wrapped them around his own hips. -"Lube babe...I don't have lube"- Gary groaned as he kissed Ash's neck and panted in pleasure since the younger boy was scratching his back.

Ash looked at Shigeru and took one of his hands, sucking on the first two digits as his eyes were glued to his boyfriend's, making him take a deep breath.

Fuck, Satoshi sucking on his fingers felt so good to Gary. His tongue moving between the fingers and his lips wrapping around them as if he was eating the best food in the world and those innocent eyes that were looking up at his were making his cock ache from how horny he was. Ash smiled at Gary and with his free hand stroked the throbbing cock of his boyfriend, knowing what he needed. -"You're so hard, Geru" - Ash breathed and took the now wet fingers out of his mouth to kneel infront of him, sucking on the tip, then taking the cock deep down his throat to lube him up.

It wasn't a proper blow job, it was simply to help since there was no lube in their hands.

-"Satoshi"- Gary let out a grunt as he looked down at the younger boy sucking him.

When Satoshi was done with his erotic semi-blow job, Shigeru fingered him until he was stretched enough and slammed his long cock inside Ash's small hole making the other gasp.

-"S-Shigeru..."- Ash held on his boyfriend's shoulder and panted at the feeling of something really big entering him, he could swear to Arceus it felt bigger than last time.

-"You okay?"- The aburn haired stopped moving.

-"E-Everytime...I swear...Everytime is like you got bigger"-

-"For some reason you get tighter, babe"- He smirked and grabbed Satoshi's hips and started pounding into him slowly, finding the bundle of nerves rather quickly and making his princess moan just as he liked him to moan.

Ash was soon a panting, sweaty mess, the dress and shoes were still on and the only thing that has come off his dress was the blue bow that was previously on his neck, it was now on the floor. His hips were jumping up and down in order to keep up with Gary but it was difficult, his boyfriend was amazing at sex and going at his pace was hard sometimes. - "G-Gary"- Ash felt lucky he was sitting on the black table and not standing up because he couldn't really feel anything else besides his ass being pounded.

-"Fuck, princess"- The older man grunted as he took Ash's thighs and lifted them higher so he could thrust deeper into him, Gary couldn't stop his hips from bucking. It felt incredibly good to be inside of Ash, he was warm and tight and sometimes Gary wouldn't pull out for hours after sex because it felt so right.

The thrusts started getting impossibly rougher and deeper, god, Satoshi could feel Shigeru pounding on his stomach for how deep he was going. His arms were now around Gary's neck, stroking his nape in the most affectionate way possible as their lips were together, he has been in love with this man since he was 5 years old and now at 18 he wasn't going to hold back into loving Gary.

Which was good because the emerald eyed would never want Ash to hold back when loving him and it was this what showed their relationship perfectly, Gary being rough and powerful, knowing where to touch Ash to make him scream and Satoshi being sweet, affectionate and gentle with touches, it made the sweet side of Gary come out in the most unexpected moments, like when they were on bed about to fall asleep and Ash decided to stroke Gary's cheeks, look into his eyes and tell him how much he loved him.

Moments like those drove Gary crazy.

\- "S-Shigeru!"- Gary heard a sweet moan coming from his princess and looked down into his eyes. - "I-I'm close"-

-"I'm close too, baby" he whispered leaning and kissing the blonde, grabbing Ash's hips posessively as he started hitting his spot repeatedly until he felt his orgasm coming closer.

-"S-Shige...Shigeru!"- Oh god that orgasm was music for Gary's ears, the way Ash would arch his back, clench his thighs and inner walls around him and lean his head back in total pleasure was better than anything Gary has seen in the world, Ash was soon releasing his cum under the skirt of the dress.

It didn't take Gary more than five minutes after it to cum inside Ash's tight hole, he didn't stop thrusting until his cock was softening. God, that felt amazing, he thought as he leaned his head on Ash's shoulder tiredly.

-"I didn't know you liked the idea of me dressed up as a girl so much"- The amber eyed whispered in a flirty tone as he stroked the auburn hair lovingly and placed a few kisses on Gary's cheeks.

-"I didn't know either, babe" - He smirked and placed a gentle kiss on Ash's shoulder.

-"You're so tired..."- Ash whispered as he moved back a little to look at Gary's face. -"You've been working so hard these past few weeks"- He was cupping Shigeru's face gently, placing kisses on his forehead, eyebrows, eyes, nose, cheeks, lips and chin and making the auburn haired relax.

-"Mhm..." - The older one mumbled while leaning into his boyfriend's sweet touch.

Ash smiled and gave him a chaste kiss on the lips while standing up from where he was, making Gary pull out and hissed when he felt some of Gary's cum slide down his thighs from his hole, but shrugged it off and started taking off his dress and shoes, cleaning the cum from his body with some baby wipes he always carried for Pikachu and once he was ready and naked, he took Shigeru to the huge bed the hotel room had to offer, laying there with Gary on his chest.

-" I love you"- Shigeru mumbled while closing his eyes and wrapping his strong arms around Ash's thin torso, resting his face against his chest and smelling the sweet scent of him.

-" I love you more Shigeru..."- Ash whispered, pulling the covers on top of them and wrapping his arms around his boyfriend's thick back, stroking it lovingly as both closed their eyes and fell asleep.

 _A/N: Well, I hope you guys liked it! I don't really know which version of Ash cross dressing to use for the next chapter. Maybe Satoshi as a maid, Satoshi as Juliet or Satoshi dressed with the dress Iris picked for him? you tell me!_

 _See you 3_


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